Triphenylphosphine → [Rac]-2-ethoxy-3-{4-[2-(5-methyl-2-phenyl-thiazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

HRID 394303

Reaktionsgleichung

Reaktionsgleichung von HRID 394303
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([O:18][CH2:19][CH3:20])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][CH:8]=1)[CH3:2].[CH3:22][C:23]1[S:27][C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:25][C:24]=1[CH2:34][CH2:35]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([O:18][CH2:19][CH3:20])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:35][CH2:34][C:24]2[N:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[S:27][C:23]=2[CH3:22])=[CH:9][CH:8]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27600182-(5-Methyl-2-phenyl-1,3-thiazol-4-yl)ethan-1-olHCID 68616503[Rac]-2-ethoxy-3-(4-hydroxy-naphthalen-1-yl)-propionic acid ethyl ester

Produkt 1

HCID 68617842[Rac]-2-ethoxy-3-{4-[2-(5-methyl-2-phenyl-thiazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In analogy to the procedure described in example 1 d], [rac]-2-ethoxy-3-(4-hydroxy-naphthalen-1-yl)-propionic acid ethyl ester was reacted with 2-(5-methyl-2-phenyl-thiazol-4-yl)-ethanol [PCT Int. Appl. (2002), WO 02/18355 A1] in tetrahydrofuran in the presence of triphenylphosphine and DIAD (diisopropyl azodicarboxylate) to yield [rac]-2-ethoxy-3-{4-[2-(5-methyl-2-phenyl-thiazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 1 e], to yield [rac]-2-ethoxy-3-{4-[2-(5-methyl-2-phenyl-thiazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid as colorless amorphous solid.

Aufarbeitung

  1. customdescribed in example 1 d

Quellen und Nachweise

ORD-Eintrag
ord-5b6397ab397c4cc59501b8d75b18cc2b
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809110B2

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